Obviously Bob Dylan isn't going to spend his 70th birthday listening to his own recordings. So I'll do it for him, while rejoicing that he is still around and willing to share the gift that opened up vistas of emotion not just for those of us lucky enough to have bought a ticket to the whole show, but for subsequent generations who find themselves responding to his shrewd insight, his sense of humour, his deep and broad love of music, and his sheer humanity.

So here's my birthday playlist: not a "best of" in any sense, even though it includes a couple of acknowledged masterpieces, but an occasionally eccentric selection of personal favourites that starts in a listening booth in a basement record shop, one summer afternoon between the Great Train Robbery and the assassination of JFK.

Let us know your own favourite Dylan song in the comments below, and we'll pull together a second playlist of 70 tracks that you've picked to celebrate Bob's birthday next Tuesday

One man's plagiarism is another man's folk process. Dylan lifts themelody of the traditional Lord Franklin, and some of its lyric tropes, to create a poignant and astonishingly mature reflection on the evanescence of youth, sketched with a few deft brush strokes. If you were 16 at the time, he strengthened the resolve to enjoy your precious time, and deepened your appreciation of it after it had gone.

2. SITTIN' ON TOP OF THE WORLD

From Victoria Spivey's Three Kings and a Queen, 1962

One of the last of the great Mississippi blues singer-guitarists, Big Joe Williams was close to his 60th birthday when the 21-year-old Dylan played harmonica and sang harmony on this version of a Mississippi Sheiks song. This Dylan would resurface 30 years later on Good as I Been to You and World Gone Wrong, two acoustic solo albums with which he reset his compass in the early-90s.

3. BARBARA ALLEN

From Live at the Gaslight, 1962

A sober rendering of the celebrated story of star-crossed lovers, delivered to a Greenwich Village audience when Dylan was parted from Suze Rotolo. The girl on the Freewheelin' cover was spending several months studying art in Italy, and it's not fanciful to imagine that you can hear how much he was missing her as he sings of the entwining of the red rose and the briar. A beautifully tender performance, in any case.

Back in the days of the folk revival it was perfectly normal for performers to sing songs in the voice of the opposite gender. Dylan goes further with this one, creating the persona of a young wife and mother in the Masabi iron range, watching her world contract and shrivel as the mining industry collapses and her husband leaves one morning without a word. This is the country Dylan grew up in, which may have helped him empathise with his subject, but the degree of identification is uncanny. "The sad silent song made the hour twice as long," is one of his most perfectly constructed and enduringly resonant lines.

Who is to say that this is not the finest of all his songs, the one in which he found the precise balance between social observation and poetry, and in which his immersion in traditional music produced his voice at its purest? Myself, I remember the chill of hearing those harmonica stabs for the first time at Sheffield's City Hall in the spring of 1965.

Recorded at four in the morning after a session that had started 10 hours earlier, and in which the musicians had done little but play cards while Dylan worked on the lyric, this draws its sepulchral power not just from the glinting ambiguities of his magnificent wordplay but from an arrangement that ebbs and flows like a slow tide. Not having been given a clue as to the length of the song, the musicians surged to a climax at the end of every chorus, only to find the singer pulling them into yet another verse. Eleven minutes and 21 seconds long, the one and only take was given its own special setting, isolated on the fourth side of a double album. It presented itself as a masterpiece, and it was.

8. I STILL MISS SOMEONE

Johnny Cash's most haunting song is performed as a duet, with Dylan providing improvised harmony and going solo on the bridge in what sounds like some only tenuously related key. To be heard in conjunction with Train of Love, Dylan's urgent and heartfelt contribution to Kindred Spirits, a Cash tribute album, a few years ago.

9. WILD MOUNTAIN THYME

Isle of Wight Festival (bootleg), 1969

He took the stage many hours late, with the Band, wearing a white suit, and delivered a underwhelming hour-long set to an audience whose expectations would have been impossible to meet. But with its thoughtful and precise phrasing, this version of a traditional ballad, part of a four-song solo acoustic interlude, provides another confirmation of how beautifully he could/can sing.

Dylan reflects his lifelong attraction to the Tex-Mex borderlands in this spare, relaxed version of a fine ballad, accompanied by his own piano and Leon Russell's bass guitar. There's also a cherishable tango-style arrangement for full band and cooing chorus on the universally reviled album called simply Dylan, thrown together by Columbia Records after his temporary defection in 1973.

With majestic accompaniment from the Band, he takes an early stab at the comfortless, darkness-falls mood that would be explored in detail almost a quarter of a century later in Time Out of Mind, his self-examination in late middle age.

All the way from Don't Think Twice, It's All Right to Sugar Baby, Dylan has been telling us that love is not a simple thing. For all its relative brevity, its ebullient attack and its jaunty harmonica, this is perhaps the most complex and multi-faceted of all his love songs, its fond and vivid reflections shot through with the deeper hues of realism. If I had to keep just one, this might be it.

Sam Shepard helped him write this epic dislocated narrative ballad, later revised, retitled Brownsville Girl and released on Knocked Out Loaded. This version doesn't have the heart-piercing line – sung in a single breath – "Strange how people who suffer together have stronger connections than those who are most content", but nor does it have the overblown production, marked by a steroid backbeat and an instrusive female chorus.

14. QUEEN JANE APPROXIMATELY

From Dylan and the Dead, 1987

I get into trouble with one prominent Dylan scholar whenever I mention this track, taken from a concert in Eugene, Oregon during a tour described by another professional Dylanologist as "one of Dylan's all-time worst career decisions". Dylan himself later wrote, in Chronicles Vol 1, that the tour had shown him a new and more stimulating angle from which to approach his music. Technically speaking, this version of Queen Jane is certainly a mess. But it's also the sound of a bunch of people, bonded by ties of affection and respect, hauling themselves out of the sludge to create something of shape and proportion and darkly luminous beauty. I can listen to it endlessly. The rest of the album is, indeed, lamentable.

15. RANK STRANGERS TO ME

From Down in the Groove, 1988

The most despised Dylan album of all contains this atmospheric arrangement of a song by the gospel composer Albert Brumley, taken from the Stanley Brothers' repertoire (also the source of A Man of Constant Sorrow, from his debut album). Just a lightly strummed guitar, Larry Klein's zooming bass, and a spectral voioce intoning a haunted lyric.

17. BOOTS OF SPANISH LEATHER

Bonus track on Japanese Not Dark Yet EP, 1998

When people say that Dylan doesn't respect his old songs, play them this. No, he doesn't follow the old tune. He's paid you, the listener, the compliment of devising an excellent set of variations, allowing him to re-engage with the lyric rather than merely trot out a classic. And you've got to love his studious attempt to fulfill a lifelong ambition to play lead guitar.

Written for the soundtrack of Gods and Generals, a Civil War TV series, this finely crafted extended ballad finds Dylan inhabiting the mind of dying soldier. The crepuscular mood is brilliantly evoked by his band, subtly invigorating each verse in a way that evokes the job the Nashville cats did on Sad-Eyed Lady. A major work, it deserved a better fate than to be tucked away on a rare-and-unreleased anthology. But then so did Blind Willie McTell.

19. SUGAR BABY

From a bayou mist of bell-like guitars and murky keyboards emerges a voice of wry wisdom. "Every moment of existence feels like some dirty trick," he sings. "Happiness comes suddenly and leaves just as quick." So this is how it ends. But, somehow, love survives.

20. IT'S ALL GOOD

At the end of an album in which he successfully channeled the Muddy Waters Blues Band of the late-50s, Dylan stands back and produces this gently barbed summary of our times: a sardonic indictment of complacency and greed. He didn't change the world, after all. But then he never really thought he could.